WO2015052264A1 - Substituted heterocyclic sulfonamide compounds useful as trpa1 modulators - Google Patents

Substituted heterocyclic sulfonamide compounds useful as trpa1 modulators Download PDF

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Publication number
WO2015052264A1
WO2015052264A1 PCT/EP2014/071593 EP2014071593W WO2015052264A1 WO 2015052264 A1 WO2015052264 A1 WO 2015052264A1 EP 2014071593 W EP2014071593 W EP 2014071593W WO 2015052264 A1 WO2015052264 A1 WO 2015052264A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
haloalkyl
halogen
compound
independently selected
Prior art date
Application number
PCT/EP2014/071593
Other languages
English (en)
French (fr)
Inventor
Huifen Chen
Yanyan CHU
Steven Do
Anthony Estrada
Baihua Hu
Aleksandr Kolesnikov
Xingyu LIN
Joseph P. Lyssikatos
Daniel Shore
Vishal Verma
Lan Wang
Guosheng Wu
Po-Wai Yuen
Original Assignee
F. Hoffmann-La Roche Ag
Genentech, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to CR20170140A priority Critical patent/CR20170140A/es
Priority to CN201480053713.2A priority patent/CN105612153B/zh
Priority to DK14789194.9T priority patent/DK3055302T3/en
Priority to LTEP14789194.9T priority patent/LT3055302T/lt
Priority to PL14789194T priority patent/PL3055302T3/pl
Priority to EP14789194.9A priority patent/EP3055302B1/en
Priority to RU2016115868A priority patent/RU2675792C2/ru
Priority to JP2016522013A priority patent/JP2016532673A/ja
Priority to RS20190254A priority patent/RS58376B1/sr
Priority to MX2016002368A priority patent/MX363457B/es
Priority to SI201431098T priority patent/SI3055302T1/sl
Priority to KR1020167012211A priority patent/KR20160064230A/ko
Priority to SG11201609411SA priority patent/SG11201609411SA/en
Priority to BR112016002012A priority patent/BR112016002012A2/pt
Application filed by F. Hoffmann-La Roche Ag, Genentech, Inc. filed Critical F. Hoffmann-La Roche Ag
Priority to CA2917193A priority patent/CA2917193A1/en
Priority to ES14789194T priority patent/ES2713323T3/es
Publication of WO2015052264A1 publication Critical patent/WO2015052264A1/en
Priority to US15/095,467 priority patent/US20160221945A1/en
Priority to HK16107470.6A priority patent/HK1219478A1/zh
Priority to US15/851,322 priority patent/US20180118680A1/en
Priority to US16/001,770 priority patent/US20180282272A1/en
Priority to HRP20190329TT priority patent/HRP20190329T1/hr
Priority to US16/657,102 priority patent/US11236046B2/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C07D207/48—Sulfur atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
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    • A61P17/00—Drugs for dermatological disorders
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
PCT/EP2014/071593 2013-10-11 2014-10-09 Substituted heterocyclic sulfonamide compounds useful as trpa1 modulators WO2015052264A1 (en)

Priority Applications (22)

Application Number Priority Date Filing Date Title
ES14789194T ES2713323T3 (es) 2013-10-11 2014-10-09 Compuestos de sulfonamida heterocíclicos sustituidos útiles como moduladores de trpa1
DK14789194.9T DK3055302T3 (en) 2013-10-11 2014-10-09 Substituted heterocyclic sulfonamide compounds useful as TRPA1 modulators
LTEP14789194.9T LT3055302T (lt) 2013-10-11 2014-10-09 Pakeistieji heterocikliniai sulfonamidiniai junginiai, tinkami naudoti kaip trpa1 moduliatoriai
PL14789194T PL3055302T3 (pl) 2013-10-11 2014-10-09 Podstawione związki heterocykliczne sulfonamidowe użyteczne jako modulatory TRPA1
EP14789194.9A EP3055302B1 (en) 2013-10-11 2014-10-09 Substituted heterocyclic sulfonamide compounds useful as trpa1 modulators
RU2016115868A RU2675792C2 (ru) 2013-10-11 2014-10-09 Замещенные гетероциклические сульфонамидные соединения, полезные в качестве модуляторов trpa 1
JP2016522013A JP2016532673A (ja) 2013-10-11 2014-10-09 Ｔｒｐａ１調節因子として有用な置換複素環式スルホンアミド化合物
RS20190254A RS58376B1 (sr) 2013-10-11 2014-10-09 Supstituisana heterociklična sulfonamidna jedinjenja korisna kao modulatori trpa1
MX2016002368A MX363457B (es) 2013-10-11 2014-10-09 Compuestos de sulfonamida heterociclica sustituida utiles como moduladores del canal del receptor de potencial transitorio a1 (trpa1).
SI201431098T SI3055302T1 (sl) 2013-10-11 2014-10-09 Substituirane heterociklične sulfonamidne spojine, uporabne kot modulatorji beljakovine TRPA1
KR1020167012211A KR20160064230A (ko) 2013-10-11 2014-10-09 Trpa1 조절제로서 유용한 치환된 헤테로환형 설폰아마이드 화합물
CR20170140A CR20170140A (es) 2014-09-12 2014-10-09 Compuestos de sulfonamida heterocíclica sustituída útiles como moduladores del canal del receptor de potencial transitorio a1 (trpa1)
BR112016002012A BR112016002012A2 (pt) 2013-10-11 2014-10-09 compostos de sulfonamida heterocíclica substituída úteis como moduladores de trpa1
SG11201609411SA SG11201609411SA (en) 2013-10-11 2014-10-09 Substituted heterocyclic sulfonamide compounds useful as trpa1 modulators
CA2917193A CA2917193A1 (en) 2013-10-11 2014-10-09 Substituted heterocyclic sulfonamide compounds useful as trpa1 modulators
CN201480053713.2A CN105612153B (zh) 2013-10-11 2014-10-09 用作trpa1调节剂的取代的杂环磺酰胺化合物
US15/095,467 US20160221945A1 (en) 2013-10-11 2016-04-11 Substituted heterocyclic sulfonamide compounds useful as trpa1 modulators
HK16107470.6A HK1219478A1 (zh) 2013-10-11 2016-06-27 用作 調節劑的取代的雜環磺酰胺化合物
US15/851,322 US20180118680A1 (en) 2013-10-11 2017-12-21 Substituted heterocyclic sulfonamide compounds useful as trpa1 modulators
US16/001,770 US20180282272A1 (en) 2013-10-11 2018-06-06 Substituted heterocyclic sulfonamide compounds useful as trpa1 modulators
HRP20190329TT HRP20190329T1 (hr) 2013-10-11 2019-02-19 Supstituirani heterociklički spojevi sulfonamida korisni za primjenu kao modulatori proteina trpa1
US16/657,102 US11236046B2 (en) 2013-10-11 2019-10-18 Substituted heterocyclic sulfonamide compounds useful as TRPA1 modulators

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201361890127P 2013-10-11 2013-10-11
US61/890,127 2013-10-11
CN2014086380 2014-09-12
CNPCT/CN2014/086380 2014-09-12

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US15/095,467 Continuation US20160221945A1 (en) 2013-10-11 2016-04-11 Substituted heterocyclic sulfonamide compounds useful as trpa1 modulators
US15/851,322 Continuation US20180118680A1 (en) 2013-10-11 2017-12-21 Substituted heterocyclic sulfonamide compounds useful as trpa1 modulators

Publications (1)

Publication Number Publication Date
WO2015052264A1 true WO2015052264A1 (en) 2015-04-16

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PCT/EP2014/071593 WO2015052264A1 (en) 2013-10-11 2014-10-09 Substituted heterocyclic sulfonamide compounds useful as trpa1 modulators

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US (4) US20160221945A1 (ja)
EP (1) EP3055302B1 (ja)
JP (2) JP2016532673A (ja)
KR (1) KR20160064230A (ja)
CN (1) CN105612153B (ja)
BR (1) BR112016002012A2 (ja)
CA (1) CA2917193A1 (ja)
DK (1) DK3055302T3 (ja)
ES (1) ES2713323T3 (ja)
HK (1) HK1219478A1 (ja)
HR (1) HRP20190329T1 (ja)
HU (1) HUE041652T2 (ja)
LT (1) LT3055302T (ja)
MX (1) MX363457B (ja)
PL (1) PL3055302T3 (ja)
PT (1) PT3055302T (ja)
RS (1) RS58376B1 (ja)
RU (1) RU2675792C2 (ja)
SG (1) SG11201609411SA (ja)
SI (1) SI3055302T1 (ja)
TR (1) TR201902249T4 (ja)
TW (1) TWI657076B (ja)
WO (1) WO2015052264A1 (ja)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016128529A1 (en) * 2015-02-15 2016-08-18 F. Hoffmann-La Roche Ag 1-(het)arylsulfonyl-(pyrrolidine or piperidine)-2-carboxamide derivatives and their use as trpa1 antagonists
WO2016133838A1 (en) 2015-02-20 2016-08-25 Rigel Pharmaceuticals, Inc. Gdf-8 inhibitors
WO2017135462A1 (ja) * 2016-02-05 2017-08-10 Ｅａファーマ株式会社 複素環スルホンアミド誘導体及びそれを含有する医薬
WO2017157885A1 (de) 2016-03-16 2017-09-21 Bayer Cropscience Aktiengesellschaft N-(cyanbenzyl)-6-(cyclopropylcarbonylamino)-4-(phenyl)-pyridin-2-carboxamid-derivate und verwandte verbindungen als pestizide pflanzenschutzmittel
WO2018015411A1 (en) * 2016-07-20 2018-01-25 F. Hoffmann-La Roche Ag Sulfonylcycloalkyl carboxamide compounds as trpa1 modulators
WO2018015410A1 (en) * 2016-07-20 2018-01-25 F. Hoffmann-La Roche Ag Bicyclic proline compounds
WO2018029288A1 (en) * 2016-08-12 2018-02-15 F. Hoffmann-La Roche Ag Sulfonyl pyridyl trp inhibitors
WO2018222795A1 (en) 2017-06-01 2018-12-06 Bristol-Myers Squibb Company Substituted nitrogen containing compounds
EP3317258A4 (en) * 2015-07-01 2019-06-26 Pharmakea, Inc. LYSYL OXIDASE LIKE 2 INHIBITORS AND USES THEREOF
WO2019164778A1 (en) * 2018-02-20 2019-08-29 Genentech, Inc. Process for preparing 1-arylsulfonyl-pyrrolidine-2-carboxamide transient receptor potential channel antagonist compounds and crystalline forms thereof
WO2022058946A1 (fr) 2020-09-18 2022-03-24 Université Grenoble Alpes Inhibition du canal trpa1 astrocytaire comme nouvelle cible therapeutique neuroprotectrice dans les phases prodromales de la maladie d'alzheimer
IT202100015098A1 (it) 2021-06-09 2022-12-09 Flonext S R L Composto antagonista del canale trpa1 per uso in patologie degenerative della retina

Families Citing this family (7)

* Cited by examiner, † Cited by third party
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JP2019019124A (ja) * 2017-07-19 2019-02-07 日本化薬株式会社 ピラジン化合物
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